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Interested in supporting critical IT infrastructure, solving complex technical challenges, and working across Windows Server environments, voice technologies, and enterprise applications? The focus is on hands-on engineers who enjoy troubleshooting, scripting, and taking ownership of reliable, secure, business-critical systems.
Location: Downtown Chicago | Hybrid – 1 Day Onsite/Week
The background
  • 3+ years of experience in systems administration, application support, voice engineering, or infrastructure engineering.
  • Strong hands-on experience with Microsoft Windows Server administration, configuration, and troubleshooting.
  • Experience with PowerShell or other scripting languages.
  • Working knowledge of voice technologies such as VoIP, SIP, IVR, telephony, or contact center systems.
  • Experience supporting and troubleshooting enterprise applications in production environments.
  • Solid understanding of networking fundamentals, firewalls, and system security.
  • Strong problem-solving skills and the ability to work independently while collaborating with technical teams.
The work:
  • Administer, configure, and support Windows Server environments and enterprise applications.
  • Develop and maintain scripts to automate processes, troubleshoot issues, and improve system operations.
  • Support voice communication technologies, including VoIP, IVR systems, dialers, and call center applications.
  • Troubleshoot server, application, voice, network connectivity, and access-related issues to ensure system reliability.
  • Contribute to Windows Server upgrades, application migrations, and security initiatives.
  • Collaborate with infrastructure, networking, and security teams to maintain stable, secure production environments.
Experience that stands out Hands-on experience with Cisco voice technologies, call center platforms, IVR scripting, or dialer systems. Familiarity with IIS, SQL Server, Windows Server migrations, or security-focused infrastructure environments is also valuable. You don't need experience with every technology listed. Strong Windows Server fundamentals, scripting ability, exposure to voice technologies, and a willingness to learn specialized systems matter most.

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Level

Senior L5

Location

Chicago, IL

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